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$599,000
6 Beds ⋅ 2 Baths
Back and Better than Ever! This custom contemporary home is nestled in one of Oconomowoc's highly desirable Fowler Lake area neighborhoods, offering an expansive 3,700+ square feet of living space, It features large bedrooms, Huge closets, two large bathrooms, double sink and dual shower heads in upper bath, and is flooded with natural light, soaring ceilings & architectural details that you don't see often! Private primary bedroom on its own level or guest quarters. Upper lofted rec rm and so much more. Enjoy a Private yard with patio, 10/10 walkability score to all that Downtown and Fowler Park/ lake loop have to offer. If you are looking for wow, come now!

727 E Madison St, Oconomowoc

Listing courtesy of Froemming Realty LLC.

$450,000
2 Beds ⋅ 1 Baths
Rarely does a property offer such exquisite craftsmanship & artistic detail while providing seemingly endless potential. Owned for decades by Master Woodworker & Fine Art Photographer Tony Casper, this amazing 2 bedroom, 1.5 bath colonial is a testament to his limitless talent & ability to create beauty, even in the most unassuming places. Whether walking up the charming front entry past his beloved Ginko, enjoying time in the custom crafted gazebo or relaxing fireside in the beechwood family/gallery room (with heated floor) built to display artifacts from world travels, Casper's creative touch is evident throughout. Make the lower studio your own space & don't miss the 15x12 office/work room off the garage!

524 E Jefferson St, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

$1,674,900
3 Beds ⋅ 2 Baths
A little bit of everything on Okauchee Lake! Modern contemporary design, nearly an acre wooded level lot and 113 feet of frontage! Plenty of room for the toys with two piers, located just off the main bay! Comfortable radiant in floor heat, new septic system, and a large 3 car garage plus additional parking!

N57W34599 Road G -, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

$749,900
4 Beds ⋅ 3 Baths
Deeded pier and boat slip on Lac La Belle - Located just steps from the heart of downtown Oconomowoc, this spacious 4-bed, 3-bath home offers the perfect blend of comfort, convenience, and lake-area living. Enjoy lake-access rights to beautiful Lac La Belle, along with a mix of shopping, creative local restaurants, and inclusive community parks within walking distance. The home boasts updated rooms and features, complemented by hardwood floors that add warmth and character throughout. The lakeside living and downtown charm make this one you cannot pass up--come take a tour today!

632 W Wisconsin Ave, Oconomowoc

Listing courtesy of RE/MAX Service First.

$479,000
3 Beds ⋅ 2 Baths
Tucked into a quiet, tranquil cul-de-sac, just a short walk to downtown shops, lakes, restaurants, parks, trails & all Oconomowoc has to offer, this beautiful mid-century ranch provides everything astute buyers expect in a quality home. With several living spaces throughout, the ''kitchen open to family room with natural fireplace'' is possibly the most sought-after floorplan designs for contemporary living and entertaining. Impressive updates such as newer cooks kitchen, and baths, as well as recent carpet in the living room and brand new carpet downstairs! Special features include: home warranty, heated garage, patio doors to private (lockable) fenced back yard and side garden shed with extra parking! See documents section for property details/updates.

677 Tulip Ct, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

$564,900
4 Beds ⋅ 2 Baths
Completely renovated 4-bedroom, 2.5-bath ranch offering 2,166 sq. ft. of stylish, move-in-ready living. The open layout is filled with natural light from abundant windows, while vaulted ceilings and skylights create an airy, inviting feel in the heart of the home. The beautifully updated kitchen features quartz countertops, soft-close cabinetry, and a cozy fireplace--perfect for gathering with family and friends. Durable LVP flooring flows throughout, providing both beauty and easy maintenance. With no basement to maintain and thoughtful updates throughout, this home offers comfort, convenience, and effortless everyday living. All of this while being just minutes from the lake and shops of Oconomowoc!

924 N Oakwood Ave, Oconomowoc

Listing courtesy of Epique Realty.

$649,900
3 Beds ⋅ 2 Baths
Timeless elegance meets modern convenience in this beautifully updated Victorian in the coveted Merchants Plat neighborhood. This exceptional home showcases exquisite original woodwork & pocket doors along with thoughtful modern updates throughout. The stunning kitchen features custom cabinetry & hardware with butcher block countertops. Upstairs are 3 spacious bedrooms, a convenient laundry in the walk-in closet & 2 full baths. The spa-like bath is complete with a classic clawfoot tub and a luxurious walk-in shower with multiple shower heads. A walk-up storybook attic on the 3rd floor is ready for your touch. Relax in the sunny sunroom or on the deck overlooking the expansive backyard. Newer windows & roof provide added peace of mind. Just steps from City Beach, downtown shopping & more.

520 W Wisconsin Ave, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

$699,900
3 Beds ⋅ 2 Baths
Near Lac La Belle and downtown, this fully updated home blends modern finishes with original character in Oconomowoc's historic Merchant's Plat neighborhood. Rare turnkey 3 bed, 2 bath home thoughtfully redone inside & out, with refinished hardwood floors, original doors & woodwork, plus a new kitchen w/ glazed painted & glass cabinetry, granite counters & SS appliances. Updates include LP siding, roof, Andersen windows, blown-in wall & foam attic insulation, electrical, plumbing, HVAC & more. LL rec/flex space, laundry & dog wash station. Outdoor living shines w/ covered porches, rear patio & beautiful floral + privacy landscaping. Just blocks from Woodland Lane Beach, paddleboard/kayak launch, City Beach, downtown Oconomowoc, shops, restaurants, parks & lake life!

102 Woodland Ln, Oconomowoc

Listing courtesy of Compass RE WI-Northshore.

$449,900
4 Beds ⋅ 2 Baths
Welcome to this well-maintained 4-bedroom, 2-bath home in a desirable location near beautiful Fowler Lake, parks, walking trails, and local amenities in the desired Oconomowoc School District. The spacious floor plan offers comfortable living with plenty of room for family, guests, or a home office. Step outside to enjoy the large backyard, perfect for entertaining, gardening, or relaxing. Whether you're looking for convenience, outdoor recreation, or a great place to call home, this property has it all. Don't miss this fantastic opportunity! Updates include: Hardwood flooring under carpet on main level. Roof 2022, Windows 2016, Garage Door 2026. Furnace and AC about 10 years.

607 Poppy St, Oconomowoc

Listing courtesy of Lake Country Flat Fee.

$324,900
3 Beds ⋅ 1 Baths
Charming 3-bedroom, 1-bath, 2-story home full of timeless character and conveniently located close to local amenities. Situated directly across from the park, this inviting home features beautiful natural woodwork, hardwood floors, spacious bedrooms, and a welcoming front porch with a low-maintenance composite deck--perfect for relaxing and enjoying the neighborhood setting. The formal dining room showcases a classic built-in china cabinet, adding warmth and functionality for entertaining or everyday living. A walk-up attic provides excellent storage or future expansion potential. Outside, enjoy a nice-sized backyard with room to relax, garden, or play. Conveniently located near shopping, dining, schools, and downtown Oconomowoc, this home offers classic appeal in a desirable location.

614 S Silver Lake St, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

$1
3 Beds ⋅ 1 Baths
Property is being sold via online auction. Auction runs July 9th thru July 30th. Rare chance to own a prime lakefront property with breath-taking views situated on a stunning 3/4-acre lot on Ashippun Lake. Here's an amazing opportunity to tear down and build your dream home! Enjoy approximately 90 feet of frontage with an expansive building envelope--ideal for constructing a substantial custom home. Existing structure is considered a tear-down, presenting a blank canvas for new construction. The entire lot is usable, flat and has no wetlands, allowing for maximum flexibility in design and footprint. Property is being sold in as-is, where-is condition. Buyer is encouraged to do their due diligence to anything pertinent to Buyer's decision.

N73W36388 S Shore Dr, Oconomowoc

Listing courtesy of HomeBuyers Advantage, LLC.

$329,000
3 Beds ⋅ 1 Baths
This 3 bedroom 1-1/2 bath home in the heart of all Oconomowoc has to offer. A very short one block to the main Lac La Belle Beach with band shell and many fun activities throughout the year. Did I also mention one block away from the amazing farmers market! The home has a main floor bedroom, a living room with a beautiful arched opening to the dining area. The kitchen has a very nice cooking/prepping area that was historically used for making candy and sold right from the amazing front porch. The home was known as the 'little red candy home.' The back of the home has a well manicured private yard. Nice sized field stone basement with a walk out rear door.

339 W South St, Oconomowoc

Listing courtesy of EXP Realty, LLC~MKE.

$249,900
2 Beds ⋅ 1 Baths
Prime location and affordability! Don't miss your chance to own this charming bungalow in the heart of Oconomowoc--perfect for a starter home or an investment property. This 2-bedroom home has an enclosed front porch for year-round enjoyment. The bathroom has been updated with heated floors and the kitchen features SS appliances. The backyard is a gardener's oasis, with garden beds already set up for planting. A little love will maximize this home's full potential. Only 2 blocks from the beach and walking distance to downtown festivals, shopping, food and more provides everything you need. Don't pass up this opportunity to own prime real estate in downtown Oconomowoc!

423 W South St, Oconomowoc

Listing courtesy of Century 21 Affiliated - Delafield.

$499,000
4 Beds ⋅ 2 Baths
Tucked away on a quiet cul-de-sac in a desirable Oconomowoc location, this character filled 4 bedroom, 2 bath cape cod is just a short walk to Fowler Lake loop and downtown amenities. Beautiful hardwood floors grace the main level, while an oversized bay window floods the living room with natural light. Updated kitchen with granite counters & new white shaker cabinetry, natural fireplace, and flexible floor plan offer both comfort and versatility. Finished lower level is perfect for entertaining! Offers a 2nd natural fireplace and groovy retro bar! Enjoy a private patio and outdoor space perfect for relaxing. Lovingly maintained and thoughtfully updated, this home blends timeless charm with modern conveniences.

1077 Christopher Ct, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

$353,000
3 Beds ⋅ 1 Baths
Charm and character is abundant in this Victorian located five blocks from the heart of downtown Oconomowoc. The main floor offers a 3-season porch, beautifully updated kitchen. The inviting living room features built-in wall gas fireplace, creating warm and relaxing for entertaining. Upper level has 3 bedrooms and main full bath. Master bedroom features a large dressing room. Spacious and fenced in yard.

725 W South St, Oconomowoc

Listing courtesy of Keller Williams Realty-Lake Country.

$479,900
3 Beds ⋅ 1 Baths
Welcome to this impeccably maintained original-owner ranch nestled within the coveted Park View Place neighborhood. Nearly 2,000 square feet of refined living space unfolds across this thoughtfully designed residence featuring 3-bedrooms and an inviting wood-burning fireplace anchoring the spacious living room. The kitchen showcases elegant oak cabinetry complemented by sophisticated Corian countertops while a reverse osmosis water system ensures quality. A convenient bonus family room enhances everyday living and the enchanting screened porch overlooks a breathtakingly private backyard on nearly half an acre. Recent updates include a 2-year-old roof, newer appliances and a 2-car attached garage with updated flooring. Close to Lily Road Park, this home awaits your discovery. Welcome Home!

1330 Christopher Ct, Oconomowoc

Listing courtesy of Victory Realty Elite.

$2,300,000
3 Beds ⋅ 4 Baths
You will find this home tucked away on a dead-end street, bordering historic Merchants Plat. With three levels of lakeside enjoyment on Lac La Belle, this home has its own sandy beach, 61.5 feet of frontage, and a boathouse renovated in 2011. The setting feels both peaceful and connected, with spaces designed for everyday living, quiet nights in, and easy gatherings. Cozy mornings and evenings are made even better by the double-sided fieldstone fireplace. At the same time, the walk-out finished lower level adds even more room to entertain with a bar, sauna, and flexible gathering space. Stroll to dining, shopping, coffee, parks, and community events, then come home to your own private spot on Lac La Belle. Don't let this rare opportunity pass you by!

904 W Labelle Ave, Oconomowoc

Listing courtesy of Stapleton Realty.

$485,000
Rare 3 family in the heart of Oconomowoc. Easy walk to downtown beach, pubs and eaterys. Home has been completely renovated in recent years including (3) new kitchens + (3) new bathrooms (see under Documents). Terrific income producer and/or owner occupied. Main level 2BR/1BA unit with (2) 1BR/1Ba upper units. Home boasts high ceilings and maintains most of its original woodwork. Extra large lot with a private fenced in back yard. 2 Car detached garage with walk up storage. Clean and dry basement has storage lockers and shared washer and dryer.

304 S Silver Lake St, Oconomowoc

Listing courtesy of Lakehomes.

$1,450,000
2 Beds ⋅ 1 Baths
Rare opportunity on sought-after Okauchee Lake with an impressive 150ft of frontage with 3 piers and beautiful lake views from nearly every room. This 2 bedroom, 1 bath home offers the chance to enjoy the lake lifestyle today while bringing your own vision and updates to the property over time. Enjoy a spacious kitchen, 2 generous bedrooms and a living room with bar and patio doors to huge deck for entertaining. The large yard offers ample space for entertaining, and the frontage is great for swimming. The garage offers added storage for lake essentials and toys. Located within walking distance to popular restaurants, bars, and nightlife, this property combines a prime location, expansive frontage, and endless potential on one of Lake Country's most desirable lakes.

N50W35096 Wisconsin Ave, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

$239,900
3 Beds ⋅ 1 Baths
Charming corner lot opportunity in Oconomowoc featuring a spacious yard and convenient location near schools, parks, shopping, dining, and downtown amenities. Property offers great potential for owner occupants, investors, or those looking to add their personal touches. Easy access to major roadways and everything the area has to offer.

803 E Lisbon Rd, Oconomowoc

Listing courtesy of Grandview Realty.

$1,900,000
Excellent opportunity to acquire a well positioned industrial complex in the heart of Oconomowoc! Wisconsin. Situated on 1.75 acres and zoned Bus Park Industrial, this versatile property comprises an 18,800 SF main bldg. and a 4,950 SF outbuilding -- totaling 23,750 SF -- ideally suited for manufacturing, warehousing, distribution, or heavy industrial operations. A standout feature is the high-voltage, high-amperage electrical service, making this property exceptionally well-equipped for power-intensive users. Strategically located at 900 Armour Rd, this site offers outstanding visibility and access in one of Waukesha County's most sought-after industrial corridors.

900 Armour Rd, Oconomowoc

Listing courtesy of Property Dynamics/Appraisal Specialists.

$650,000
4 Beds ⋅ 4 Baths
Welcome to a home designed for living, entertaining, and making memories. The spacious kitchen offers plenty of room to cook and gather, opening to a stunning great room with cathedral ceilings, a natural fireplace, and access to a relaxing three-season room. Living and dining rooms provide additional space for hosting. Upstairs features three bedrooms and three full baths, including a primary suite with whirlpool tub, vanity, and tiled shower, plus a second bedroom with en-suite. The finished lower level offers a rec room, fourth bedroom, full bath, and office. Set on a great lot with a zip line and Upper Oconomowoc lake access- this home delivers space, comfort, and lifestyle.

N51W35827 Hillcrest Ct, Oconomowoc

Listing courtesy of Shorewest Realtors, Inc..

$699,900
A free standing 5,751 SQ FT building, located in a prime Downtown Oconomowoc location. Zoned Commercial/General has significant redevelopment potential for a mixed use/tenant income investment opportunity. This property is 100 years old and has great bones, with potential wood beam exposure in ceiling and exposed brick to create a ''cool'' industrial look. New roof installed May, 2026. Sale includes real estate only (land/improvements).

111 S Main St, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

$424,900
Move-in ready office in a highly visible diverse use location in the heart of Lake Country. Blocks from Okauchee Lake, this nicely maintained handicap accessible building has 4 offices, reception area, kitchen, bath, file room & full lower for ample storage. Natural & gas stone fireplace hi-lites the main office. Parking for 15+ cars & 2.5 car garage w/motion lighting, key pad & new garage door. Recently updated doors, flooring, paint, siding, bath, tile, furnace, water softener, gutter guards, siding, chimney, concrete & asphalt extra wide drive. Foundation has been professionally waterproofed with transferable warranty! All set on a appx. 1/2 ac lot w/mature trees & plantings. Lawn serviced by Natural Lawn Care Service of America. Zoned, SF, low density, rental, commercial, investment

N50W34710 Wisconsin Ave, Oconomowoc

Listing courtesy of First Weber Inc - Delafield.

$1,199,000
3 Beds ⋅ 1 Baths
The main and lower level of this home have multiple sliding doors for quick access to a large wrap around deck. An extra large living room faces the lake and with the addition of headers the owner has made it possible to make the main floor open concept. The upper level is comprised of 3 bedrooms and a full bath. Exceptional 75 feet of level frontage for enjoyment of the lake! Build a boat house if you'd like. Multiple piers have been here for decades. Lots and lots of parking, A large garage with a spancrete floor giving you plenty of room in the lower level for storage or more fun space.

N53W34956 Road B -, Oconomowoc

Listing courtesy of Berkshire Hathaway HS Lake Country.

Source of listing data: Metro MLS. Copyright 2026 Multiple Listing Service, Inc. - All Rights Reserved. Information is supplied by seller and other third parties and has not been verified. IDX information is provided exclusively for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.